Process for producing a polyoxyalkylene compound

Abstract

The present invention has an object of producing a polyoxyalkylene compound by ring-opening polymerization of an alkylene oxide to a certain specific highly hydrophobic initiator. The present invention provides a process for producing a polyoxyalkylene compound, characterized in that the polyoxyalkylene compound is produced by ring-opening polymerization of an alkylene oxide, in the presence of a plural metal cyanide complex catalyst, with an initiator selected from an organopolysiloxane compound having an active hydrogen-containing functional group to which an alkylene oxide is reactive, and a fluorine-containing compound having such an active hydrogen-containing functional group and a fluorinated hydrocarbon group.

What is claimed is: 
     
       1. A process for producing a polyoxyalkylene compound, comprising ring-opening polymerizing an alkylene oxide, in the presence of a plural metal cyanide complex catalyst, with an initiator selected from the group consisting of an organopolysiloxane compound, wherein said organopolysiloxane compound is a polymer of a siloxane having at least one organic group bonded thereto and wherein at least one of said organic groups is an organic group having an active hydrogen-containing functional group, and a fluorine-containing compound selected from the group consisting of a compound of one of the following chemical formulae (4) to (8):   R.sub.f.sup.1 --R.sup.11 --X.sup.2                         (4),       R.sub.f.sup.1 --COOX.sup.3                                 ( 5),       R.sub.f.sup.1 --CON(R.sup.14)--X.sup.3                     ( 6),       X.sup.2 --R.sup.12 --R.sub.f.sup.2 --R.sup.13 --X.sup.2    ( 7) and       (R.sub.f.sup.1).sub.t --C.sub.6 --F.sub.5-t --X.sup.2      ( 8)     wherein X 2  is an active hydrogen-containing functional group selected from the group consisting of --OH, --SH, --NH 2 , --NHR 14  and --CO 2  H, or a hydrocarbon group having at least one such functional group, X 3  is a hydrogen atom or a hydrocarbon group having at least one of the above active hydrogen-containing functional groups, R 14  is a hydrogen atom or a C 1-6  hydrocarbon group, R f   1  is a perfluoroalkyl group of at least one carbon atom, R f   2  is a perfluoroalkylene group of at least 2 carbon atoms, R 11  is an alkylene group containing no fluorine atom, each of R 12  and R 13  which are independent from each other, is an alkylene group containing no fluorine atom, and t is 0 or an integer of from 1 to 3.   
     
     
       2. The process according to claim 1, wherein the alkylene oxide is a C 2-4  alkylene oxide. 
     
     
       3. The process according to claim 1 wherein the active hydrogen-containing functional group is a functional group selected from the group consisting of a hydroxyl group, a mercapto group, a primary amino group, a secondary amino group and a carboxyl group. 
     
     
       4. The process according to claim 1, wherein the reaction is conducted in a solvent. 
     
     
       5. The process according to claim 1, wherein the organopolysiloxane compound is at least one member selected from the group consisting of a compound of one of the following chemical formulae (1) to ##STR6## wherein X 1  is a C 3-10  hydrocarbon group containing at least one functional group of at least one type selected from the group consisting of --OH, --SH, --NH 2 , --NHR 10  and --CO 2  H, which can optionally contain an ether bond, a thioether bond or an amino bond, R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 8  and R 10  are, respectively, the same or different C 1-6  hydrocarbon groups, R 5  and R 9  are C 1-18  hydrocarbon groups, n is 0 or an integer of from 1 to 200, and m is an integer of from 1 to 10. 
     
     
       6. The process according to claim 5, wherein the organopolysiloxane compound is a polydimethylsiloxane compound wherein each of R 1  and R 2  is a methyl group. 
     
     
       7. The process according to claim 5, wherein X 1  is a hydroxyalkyl group, a dihydroxyalkyl group, a hydroxyalkoxy-substituted alkyl group, a mercaptoalkyl group, an aminoalkyl group, an N-aminoalkyl-substituted aminoalkyl group or a carboxyalkyl group.